HCID 19769121, compound → HCID 19769118, compound

HRID 2081537Notes

Reaction equation

HRID 2081537 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[C:12]1[C:13]([O:29]CC2C=CC=CC=2)=[N:14][C:15]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:16]([CH2:18][CH3:19])[CH:17]=1>O1CCCC1.CO.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13](=[O:29])[NH:14][C:15]([CH2:20][O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:16]([CH2:18][CH3:19])[CH:17]=1

Participants

5

Reactant 1

HCID 19769121HCID 19769121, compound

Product 1

HCID 19769118HCID 19769118, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis/trans 3-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-benzyloxymethyl-2-benzyloxypyridine (1.40 g, 2.94 mmol) in dry tetrahydrofuran (20 mL) and methanol (15 mL) containing 10% Pd on charcoal (215 mg) as a catalyst was hydrogenated at atmospheric pressure for 20 hours. The catalyst was filtered off and the solution evaporated to give a white residue. This residue was triturated with diethyl ether to give pure product with m.p. of 140°-142° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solution evaporated
  3. customto give a white residue
  4. customThis residue was triturated with diethyl ether
  5. customto give pure product with m.p. of 140°-142° C.

Sources & evidence

ORD record
ord-1fb7fb39939b42f8ad5f38d9f717556a
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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